Document Detail

Triflic acid-catalyzed additions of 2-alkoxycarbonyl allylboronates to aldehydes. Study of scope and mechanistic investigation of the reaction stereochemistry.
MedLine Citation:
PMID:  17288375     Owner:  NLM     Status:  PubMed-not-MEDLINE    
The substrate scope and the effect of substrate on the observed inversion of stereoselectivity in the triflic acid-catalyzed allylboration reaction between 2-alkoxycarbonyl allylboronates and aldehydes are presented. A mechanistic investigation is described so as to confirm the involvement of a carbocation intermediate as the source of stereochemical inversion. This methodology allows a facile access to beta,gamma-disubstituted five-membered ring lactones with an exo-methylene at the alpha-position.
Tim G Elford; Yuichiro Arimura; Siu Hong Yu; Dennis G Hall
Related Documents :
21956575 - Nutritional value of d: -amino acids, d: -peptides, and amino acid derivatives in mice.
12398515 - Catalytic hunsdiecker reaction of alpha,beta-unsaturated carboxylic acids: how efficien...
16018635 - Synthesis and fluorescence spectra of oxa[3.n]phenanthrenophanes.
18302005 - First results of the rambas experiment on investigation of the radiation mechanism of c...
15062815 - Carbonic acid enhancement of hydrolysis in aqueous pretreatment of corn stover.
23947005 - Minocycline, but not ascorbic acid, increases motor activity and extends the life span ...
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  72     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2007 Feb 
Date Detail:
Created Date:  2007-02-09     Completed Date:  2007-04-17     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1276-84     Citation Subset:  -    
Department of Chemistry, University of Alberta, Edmonton, Alberta, Canada T6G 2G2.
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

Previous Document:  Convenient synthesis of unsymmetrical organochalcogenides using organoboronic acids with dichalcogen...
Next Document:  Kinetics of the reactions of [p-nitrophenoxy(phenyl)carbene]pentacarbonylchromium(0) with aryloxide ...